AGREE!!! That is a definite conflict of interest. I'm sure your by-laws even state something to the effect.

Read your condo docs and your state's association laws. It may not be illegal to hold both positions but should have been handled better.

Normally one Board member alone does not have the authority to enter into contracts on behalf of an Association; however, if the Board voted and he merely singed as its agent, then that would be allowable. Further, the Declaration or Bylaws may prohibit a Board member from contracting with the Association. There are several possible irregularities in the described situation.

This is an obvious "conflict of interest." Your president has no sensitivity to the appearance of making himself handyman. Or he just doesn't care what you think.  
After you and a few other owners speak to him (nicely, please) if he doesn't give up the post then get rid of him at the first chance.

What benefits? Sounds like your HOA is too generous, no matter whom holds the position.  
 
If he is competent and charges a competitive fee, you should be pleased. However, many states do not permit directors to be paid, so if yours is one of them, he will have to make a decision as to which position he wants.

We had somehting like this at out Condo. The pres thought it was okay to hire his girlfriend to work in the office. Eventually we got rid of her when she did some really ftuped thinks.  
but it still makes a lot of the pool ladies maid.

Obvious small time crook. I'd check the books. Or is his brother your accountant?

Larry Davis: what makes you think that it's wrong to be generous and offer benefits? Doesn't everyone deserve to have health benefits and a pension? Or are some people less than human and undeserving?

I thought for a minute you lived in my complex-then I remembered we got rid of that jerk (I cleaned that description up quite a bit). 
One of our past presidents (call him A) hired himself as the landscaper. His girlfriend (Call her B) who was also on the board as the secretary, had a best friend (call her C) whom he hired as the "arborist" who in turn hired B to help trim all of our beautiful, mature flowering bushes and trees. A and B then hired an old high school buddy (call him D) to do all of the repair and maintenance. 
The result of this was: we lost over 50% of our plantings due to unskilled trimming by A,B and C, our in-ground sprinkler is now rendered useless since it was never serviced by A,B, or C, the grass died, and the high school buddy D bragged to my carpenter doing work in my unit that he made $250,000.00 off of our complex in a short period or time. No, they are no longer on the Board and anyone who dealt with them has nothing nice to say. We believe they also had work done, windows installed, and carpentry work done on our dollar by the high school buddy, but all records seem to have disappeared on that front. 
My point is, get this guy off the Board as president. That is a conflict of interest if there ever was one and a mishandling of the duties of office for sure.

This situation may or may not violate the by-laws, Master deed or state law.  
On the other hand it may be a great deal for the association.  
In our condo association the by-laws says that any member of the BOD cannot get paid as a BOD. But there is NOTHING in any by-law or state law preventing the BOD from hiring that person as handyman. All it would take is 2 of the 3 BOD members we have to vote yes. 
The laws and by-laws vary from association to association and state to state, so this arrangement may not be strictly legal in some associations. Nevertheless, you might see what he is charging compared to what he is doing. It might be cost effective even if it violates your by-laws.

Another Voice. we had similar at our condo as i explaned above. there is such a good feeling when we got rid of them on the board. but they are still in the condo and when we see them at the pool we get desgusted. woudent you think they would be ashamed? their not smart enough to be ashamed. Sally

The Board is given the responsibility to hire and fire. Check if they gave approval. Make sure the Assn carries workman's comp insurance too. If he gets hurt, he can sue his own Assn. If there is insurance, premiums will go up on a claim. Hence, the conflict. Ask your State Condo board for help here.

better check with your insurance carrier 
and also his insurance carrier who will pay if  
injuries happen

Nip this quickly in the bud. The board president does not get to serve as dictator of the bod.  
 
Nothing good can come of this, and it is doubtful that this is legal in any state. Certainly check your docs, i doubt if your board presidents actions will be found permissible. 
 
A bid must be taken on such matters by the bod, not the president only. In order for a president to be paid, it has to be written in the docs, and in most cases voted on by a certain number of owners. 

The bright side of this discussion is that so many readers joined in. A moral to the story is that owners should not wait until the ship is going over the waterfall. As soon as it enters the rapids is when action should be taken.

Brief Troubleshooting guide. 
1) In the event of a Condo or HOA problem: 
the complainer (potential plaintiff) should send a certified letter to the BOD 
2) the complainer (potential plaintiff) should study the applicable state laws in his or her jurisdiction, and b) read the association original declarations, conditions, covenents and restrictions, the Master Deed and By-laws 
3) If applicable talk to , email write all his fellow unit owners, 
4) try talking or negotiating directly with all the BOD members 
5) at last resort, and if the law and by-laws are on his side, send registered letters to all the BOD. 
6) threaten to go to an attorney, again with certified letters with all the BOD 
7) engage an attorney and attempt mediation and negotiation 
8) Last resort litigation

This is usually legal though that doesn't make ethical or right. It is way over the line of common sense. It is a brazen violation of best practices and should be ended immediately.  
The President concerned should be shown this chain of remarks about his behavior.

Is he doing a better job and is he cheaper than the previous handy man? 
 
Victor

"Is it legal for a President to fill the position without all the owners voting." Yes. 
 
The Board of Directors is appointed to conduct the HOA's business. Part of that is to review bids for contractors and vote, based on whatever criteria and requirements the Board agrees to, to approve one. HOA members (owners) do not get involved in this process unless the Board votes to do so. 
 
In your case, since the President was presumably one of the bidders, proper ethics was followed. The only way to confirm that is to request of the Board to view the minutes of when the vote was taken. The minutes should reflect that the President abstained from voting. If in fact the President did abstain, then there is nothing else to do, it is a done deal. If there is no record of the President abstaining then there are several avenues that could be taken but to know specifically you will need to refer to Robert's Rules, the HOA governing documents, and the laws of your state. 
 
Note: Bids presented to your Board of Directors are considered confidential and as such no HOA member (owner) should expect to review those bids.  
 
With the President, or any Board member, as contractor for their HOA there is always the possibility for 'conflict of interest' but as long as the President abstains on any vote that affects the handyman position and it is recorded in the meeting minutes all should be fine. 
 
Our maintenance man has been in that position for over two years. During that time frame he was President of the HOA and is now our Vice-President. We have no problems.

What do your governing documents say? They should have a clause about board members are not permitted to be paid for services by the Association. That should also include any business they might own.  
Also, unless you are a board member you should not have access to the bid provided to your association. Someone needs to also make sure all contractors have the proper credentials to work on your property such as a current paid up policy for Workers Comp and liability insurance.

This is without a doubt a Conflict of Interest.

Our president did one better.  
 
He volunteered to do some simple handyman work (fix mailboxes, change lightbulbs, pick up trash and other basic tasks) and he felt that by him doing such simple labor would save the association over having the regular handyman doing it.  
 
After a year or so, he decided that his time was worth money and advised the property manager that the board voted that he would be paid, and that he was still cheaper than the regular guy. Truth was that the board knew nothing of this, much less vote to approve it. 
 
As our bylaws state that boardmembers are volunteers and do not get paid, he secretly had the property manager make the checks payable to his wife to cover it up, knowing that it would be buried in some 50 pages of monthly management reports that nobody really looks at.  
 
It was found by a diligent boardmember and the president resigned. 
 
It takes all kinds.